Proacetylenic reactivity of a push-pull buta-1,2,3-triene: New chromophores and supramolecular systems

Yi Lin Wu, Francesca Tancini, W. Bernd Schweizer, Daniela Paunescu, Corinne Boudon, Jean Paul Gisselbrecht, Peter D. Jarowski, Enrico Dalcanale, François Diederich*

*Corresponding author for this work

    Research output: Contribution to journalArticlepeer-review

    21 Scopus citations

    Abstract

    Proacetylenic: An aniline-based donor-acceptor-substituted butatriene exhibits not only cumulene-like dimerization to give a [4]radialene (λ max=756 nm), but also acetylene-like (proacetylenic) reactivity towards tetracyanoethene, affording via [2+2] cycloaddition- cycloreversion a NIR-absorbing zwitterionic chromophore (λ max= 825 nm). The cationic charge on the imminium-type nitrogen in the zwitterion is evidenced by host-guest complexation with a tetraphosphonate cavitand.

    Original languageEnglish (US)
    Pages (from-to)1185-1190
    Number of pages6
    JournalChemistry - An Asian Journal
    Volume7
    Issue number6
    DOIs
    StatePublished - Jun 2012

    Keywords

    • proacetylenic
    • push-pull chromophore
    • radialene
    • self-assembly
    • zwitterions

    ASJC Scopus subject areas

    • Biochemistry
    • Organic Chemistry

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